CN1102757A - 活性化合物的胶体分散液剂 - Google Patents
活性化合物的胶体分散液剂 Download PDFInfo
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- CN1102757A CN1102757A CN94117633A CN94117633A CN1102757A CN 1102757 A CN1102757 A CN 1102757A CN 94117633 A CN94117633 A CN 94117633A CN 94117633 A CN94117633 A CN 94117633A CN 1102757 A CN1102757 A CN 1102757A
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Classifications
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08L39/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
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Abstract
本申请涉及在活性化合物制剂中应用基于乙烯
基吡咯烷酮的聚合物,该活性化合物是少量溶于水
的,且适宜时,少量地溶于非极性溶剂。
Description
本发明涉及在活性化合物的制剂中应用基于乙烯基吡咯烷酮的聚合物,该活性化合物少量溶于水,且适宜时少量地溶于非极性溶剂。
活性化合物的生物效力及由此而来的活性作用在很大程度上取决于其溶解性。一般说来,活性化合物仅在溶解的形式下才能表现生理作用。因此,用微溶的活性化合物提供的活性组合物给药或施用经常出现困难。
人们试图增加微溶活性化合物的生物效力,并因此通过选择不同剂型来降低需要的剂量,这些剂型既改进活性化合物的水溶性也改进其溶解速度。
在美国专利US-4 412 986中,通过制备与水互溶聚合物,如与聚乙烯基吡咯烷酮(PVP)共沉淀的非结晶性的活性化合物,大大提高了活性物质的溶解度,这是因为共沉淀物溶解后,活性化合物可以过饱和形式存在相当长的时间。PVP可与其他赋形剂结合广泛用于配制对结晶作用稳定的活性化合物的水制剂,所述其他赋形剂如表面活性剂。在EP 212 853 A2、JP 04 018 015、JP 04 018 022、JP 04 149 132、JP 03 287 535和JP 02 264 716中描述了含有PVP的苯妥英或富马酸氯苯苄咯、吡氧噻嗪、炔烃雄烯唑、双吡苯丙酸或tranilast溶液制品。
另外,通过从有机活性化合物溶液中沉淀的方式制备胶体分散液的过程也被描述过。颗粒大小<0.1μ的胶体水分散液,也称作水溶胶,原则上可通过沉淀的方法生产。例如Basle大学的M.List在出版于1987的学术论文“Hydrosols,an intravenous drug form for the preparation of injections and infusions of active compounds which are sparingly soluble in water”中叙述了可以静脉给药的胶体分散液的制备。该分散液通过使微溶于水的活性化合物在与水混溶的有机溶剂中的溶液与水相混合而制得,有机相和水相两相中都可能含有稳定剂和其他添加剂。US 4 826 689 中描述了通过向活性化合物在纯的或含有助溶剂的有机相的溶液中,控制性地加入稳定剂水溶液制备单分散胶体分散液的过程,适宜时,分散液的质量在很大程度上由制备条件决定,如釜体积,温度以及搅拌和计量速度。根据DD 293 727A,活性化合物2-羟基-5-甲基-月桂苯酮的胶体分散液可通过采用PVP作为稳定剂的方法来制备。
可是,上述先有技术中的制剂的原理具有一些缺点。尽管其沉淀在溶于水后会形成活性化合物的过饱和溶液,在大多数情况下,过饱和度较低。而且,经过一段时间过饱和溶液会再次析出结晶,这对活性化合物的生物效力存在不利影响。活性化合物的使用也变得困难。因此,例如,施用植物保护组合物水剂时,通常使用的喷雾器中存在数个过滤器和喷嘴。在施用固体活性化合物水喷雾液的过程中,所有这些滤器和喷嘴可很容易地被结晶出的活性化合物堵塞,其严重程度或大或小。
通过有机溶液中的沉淀作用制备具有明显结晶倾向的活性化合物胶体分散液的一个重要因素,是在沉淀后以非结晶形态存在的颗粒直接转化成热力学更稳定的结晶相。在US 4 826 689中,通过控制沉淀条件,活性化合物以这种非晶形态的亚稳态维持稳定一定时间。但是该专利说明书中提到需要从分散液介质中分离出沉淀产物,随后使之干燥,以避免非结晶形的活性化合物的颗粒重结晶。为了制备对颗粒大小稳定的水溶胶,沉淀后必须除去溶剂。Basle大学的P.Gassmann在1990年出版的首次学术论文“Preparation and stabilization of hydrosols for intravenous administration”中说明在制备单独的活性化合物和同类物质的水溶胶的情况下,其稳定性大大信赖于单个物质的结构和物理化学特性。采用二氢吡啶类的darodipine 和 isradipine的实验结果证明isradipine 水溶胶比对比的isradipine水溶胶最高稳定20倍。
从现有技术中可以看到,基于现有的制剂原理和在这种情况下使用的制剂助剂而制得的微溶性活性化合物制剂,它们以好的活性和好的使用性质而显得突出,它们的制备是甚为困难的。可是,与制剂有关的活性增强使得需要的活性化合物的剂量降低,结果导致更少的副作用和更少的环境污染。
本发明涉及在水微溶性活性化合物的制剂中使用含有疏水共聚单体的乙烯基吡咯烷酮和/或乙烯基已内酰胺共聚物。
在水介质中,制剂形成均匀的溶液或胶体分散液,与常见的活性化合物的水剂相比,本制剂稳定性明显增加,使用性质更好且活性更强。
本发明的制剂除了活性化合物(A)外主要还含有乙烯基吡咯烷酮和/或乙烯基已内酰胺乙烯基酯聚合物(B),表面活性剂(C)和(如果适宜)添加剂(D)和/或溶剂(E)。
在本发明中的共聚物(B)是至少一种乙烯基吡咯烷酮和/或乙烯基已内酰胺和疏水性乙烯基单体的无规共聚物。这些乙烯基单体的实例是,高级环状乙烯基-内酰胺类,核烷基化的乙烯基吡咯烷酮、乙烯基已内酰胺、乙烯基酯类,乙烯基醚类,萜烯,马来酸酐和马来酸与直链或支链醇的单一或双酯。特别优选以下整数通式的乙烯基吡咯烷酮和乙烯基酯的无规共聚物。
其中x为0-16之间的整数,优选为0-6,且n和m大于1,优选大于10,且乙烯基酯在全部聚合物中的重量含量为5-90%,优选为10-80%,且特别优选为30-80%。
以乙烯基吡咯烷酮为基础的这些共聚物本身是仅少量溶于水或甚至不溶于水的。因此益发令人惊奇的是这些共聚物可用于制备活性化合物的水分散液或溶液,且由此产生的稳定性好于含有(例如)可溶于纯水的聚乙烯基吡咯烷酮或仅含有表面活性剂作稳定剂的已知标准制剂。
在本发明中可能使用的表面活性剂(C)为非离子型、阳离子型和阴离子型乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚、烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、烷基芳基磺酸盐和芳基硫酸盐。上述表面活性剂的实例列于助剂词典中(Fiedler, H.P.“Lexikon der Hilfsstoffe fur Pharmazie,Kosmetik und angrenzende Gebiete”,Cantor Aulendorf (1981))。它们可单独使用或也可作为混合物使用。在本发明中特别适合的表面活性剂是离子型表面活性剂,如十二烷基硫酸钠和二辛基磺基琥珀酸钠和十二烷基苯磺酸单乙醇胺盐。
当本发明的制剂为植物保护活性化合物制剂时,制剂中的添加剂(D)为低温稳定剂和粘着促进剂,它们分别在低温时改进制剂的贮藏性质和对从制剂制备的水喷雾液在植物上的附着起促进作用。低温稳定剂的实例为脲、甘油和丙二醇。可能的粘着促进剂优选的是羧甲基纤维素,天然存在的和合成的聚合物,如阿拉伯胶、聚乙烯醇、聚乙酸乙烯酯和天然存在的磷脂,如脑磷脂和卵磷脂,以及合成磷脂。
可使用的溶剂(E)为通常可使用于这类目的的所有极性和非极性溶剂。可用的溶剂为丙二醇,各种分子量的聚乙二醇;酮类,如甲基异丁基酮和环己酮;和酰胺类,如二甲基甲酰胺;环状化合物,如N-甲基-吡咯烷酮,N-甲基已内酰胺和丁内酯;且也可以是强极性溶剂如二甲基亚砜;和芳烃,如二甲苯;酯类,如丙二醇单甲醚-乙酸酯、已二酸二丁基酯、乙酸已酯、乙酸庚酯、柠檬酸三正丁基酯和邻苯二甲酸二正丁酯;二醇醚类,如丙二醇甲基醚;醇类,如乙醇、正-和异丙醇、正和异丁醇、正和异戊醇、苄醇、四氢糠醇和1-甲氧基-2-丙醇。特别优选的溶剂是正甲基吡咯烷酮,二甲基甲酰胺,二甲基亚砜,丙二醇,聚乙二醇,乙醇和异丙醇。
原则上本发明的制剂可使用于所有药物。可是它们特别适合于在室温下在水中溶解度<0.5g/100ml,特别是<0.1g/100ml且更具体的是<0.01g/100ml的活性化合物(A)。上述活性化合物的实例为二氢吡啶类如,例如,硝苯吡酯、硝苯吡啶、硝吡乙甲酯、硝吡丁甲酯、darodipine、isradipine和felodipine。
其它活性化合物的实例是如下述的农药:
杀真菌剂:
2-苯胺基-4-甲基-6-环丙基-嘧啶;2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-羧-N-甲酰胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧亚氨基-N-甲基-2-(2-苯氧苯基)-乙酰胺;8-羟基硫酸喹啉;甲基-(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧基]-苯基}-3-甲氧丙烯酸酯;甲基-(E)-甲氧亚氨基[α-(O-甲苯氧基)-O-甲苯基]乙酸酯;2-苯基苯酚(OPP),Aldimorph,Ampropylfos,敌菌灵、戊环唑、苯霜灵、麦绣灵、苯菌灵、乐杀螨、联苯酚、双苯三唑醇、灭瘟素、糠菌唑、粉病定、敌菌丹、克菌丹、多菌灵、萎绣灵、灭螨猛、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氯、环唑醇、酯菌胺、双氯酚、苄氯三唑醇、Diclofluanid、哒菌清、氯硝胺、乙霉威、醚唑、甲菌定、烯酰吗啉、烯唑醇、敌螨普、二苯胺、Dipyrithion、灭菌磷、二噻农、多果定、敌菌酮、克瘟散、Epoxyconazole、乙菌克、氯唑灵、异嘧菌醇、Fenbuconazole、呋菌胺、种衣酯、拌种咯、苯绣啶、丁苯吗啉、薯瘟锡、毒菌锡、福美铁、嘧菌腙、氟啶胺、Fludioxonil、氟菌安、Fluquinconazole、氟硅唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、Fosetyl-Aluminum、四氯苯酞、麦穗宁、呋氨丙灵、拌种胺、双胍盐、氯苯嘧啶醇、已唑醇、土菌清、烯菌灵、酰胺唑、双胍辛醋酸盐、iprobenfos、异丙定、富士一号、春雷霉素、锰铜混剂、代森锰锌、代森锰、嘧菌胺、灭绣胺、氨丙灵、Metconazol、磺菌威、甲呋菌胺、代森联、嘧菌胺、腈菌唑、福美镍、异丙消、环菌灵、甲呋酰胺霜灵、Oxamocarb、氧化萎绣灵、稻瘟酯、戊菌唑、戊醇隆、Phosdiphen、多马霉素、粉病灵、多氧霉素、噻菌灵、丙氯灵、杀菌利、百维灵、丙环唑、甲基代森锌、定菌磷、啶斑肟、Pyrimethanil、毛醌素、五氯硝基苯、戊唑醇、白叶减、四氯硝基苯、氟醚唑、涕必灵、噻菌腈、甲基托布津、福美双、甲基立枯磷、对甲抑菌灵、唑菌酮、唑菌醇、唑菌嗪、杨菌胺、三环唑、克啉菌、氟菌唑、嗪氨灵、Triticonazol、有效霉素、烯菌酮、代森锌、福美锌。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、乙酰甲胺磷、氟硝菊酯、棉铃威、涕灭威、甲体氯氰菊酯、虫螨脒、AZ 60541、Azadirachtin、谷硫磷、乙基谷硫磷、唑环锡、苏云菌杆菌、4-溴-2-(4-氯苯基)-1-(乙氧甲基)-5-(三氟甲基)-1H-吡咯-3-甲腈、虫威、丙硫克百威、杀虫磺、氟氯氰菊酯、氟氯菊酯、丁苯威、Brofenprox、溴硫磷、全杀威、噻嗪酮、丁叉威、哒螨酮、硫线磷、西维因、呋喃丹、三硫磷、丁硫克白威、杀螟丹、Chloethocarb、Chlorethoxyfos、Chloretoxyfos、毒虫畏、定虫隆、氯甲磷、N-[(6-氯-3-吡啶基)-甲基]-N′-氰基-N-甲基乙亚胺酰胺、毒死蜱、甲基毒死蜱、顺-苄呋菊酯、Clocythrin、四螨嗪、杀螟腈、乙氰菊酯、三氟氯氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、内吸磷、内吸磷硫赶式异构体、甲基内吸磷、杀螨隆、二嗪农、除线磷、敌敌畏、Dicliphos、百治磷、乙硫磷、氟脲杀、乐果、甲基毒虫畏、敌杀磷、乙拌磷、克瘟散、Emamectin、高氰戊菊酯、苯虫威、乙硫磷、醚菊酯、氯嘧啶磷、克线磷、喹螨磷、杀螨锡、杀螟松、Fenobucarb、苯硫威、双氧威、分扑菊酯、Fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、Fipronil、氟啶胺、Fluazuron、唑螨脲、氟氰戊菊酯、氟虫脲、Flufenprox、氟胺氰菊酯、地虫磷、安果、噻唑硫磷、Fubfenprox、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、咪蚜胺、Iprobenfos、异唑磷、丙胺磷、异丙威、异噁唑磷、Lamda-三氟氯氰菊酯、Lufenuron、马拉硫磷、灭蚜磷、Mervinphos、甲丙硫磷、多聚乙醛、虫螨畏、甲胺磷、杀扑磷、灭虫威、灭多威、Metolcarb、Milbemectin、久效磷、Moxidectin、二溴磷、NC 184、Nitenpyram、氧化乐果、甲叉丙威、风吸磷、Oxydeprofos、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、虫螨磷、乙基虫螨磷、溴丙磷、猛杀威、丙虫磷、残杀威、丙硫磷、发果、Pymetrozin、吡唑硫磷、哒嗪硫磷、反灭菊酯、除虫菊、哒螨酮、Pyrimidifen、蚊蝇醚、喹硫磷、杀抗松、克线丹、Silafluofen、治螟磷、乙丙硫磷、Tebufenozide、Tebufenpyrad、Teburimimphos、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁磷、杀虫威、Thiafenox、硫双灭多威、特氨叉威、甲基乙拌磷、治线磷、四溴菊酯、Triarathen、三唑磷、Triazuron、敌百虫、Triflumuron、Trimethacarb、蚜灭多、二甲威、Xylylcarb、Zetametrin。
除草剂:
N-酰苯胺类除草剂如吡氟草胺、敌稗;芳基羧酸类如二氯甲基吡啶酸;麦草畏、毒莠定;芳基氧链烷酸如2,4-滴,2,4-滴丁酸,2,4-滴丙酸、氟草定、2甲4氯、2甲4氯丙酸、绿草定;芳基氧苯氧链烷酸酯如禾草灵、恶唑禾草灵、精吡氟禾草灵、盖草能、喹禾灵;连氮酮类如杀草敏、达草灭;氨基甲酸酯类如氯苯胺灵、异苯敌草、甜菜宁、Propham;氯乙酰苯胺类如甲草胺、乙草胺、去草胺、吡草胺、乙基乙草胺、丙草胺、扑草胺;二硝基苯胺类如胺磺灵、胺硝草、氟乐灵、二苯醚类如氟锁草醚、甲羧除草醚、乙羧氟草醚、氟磺胺草醚、Halosafen、克阔乐、氟硝草醚、脲类如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆、甲基苯噻隆、羟胺类如枯杀达、稀草酮、噻草酮、稀禾定、肟草酮;咪唑类如普杀特、咪草酯、灭草烟、灭草喹;腈类如溴苯腈、敌草腈、碘苯腈;氧乙酰胺类如苯噻草胺;磺酰脲类如 Amidosulfuron、苄嘧磺隆、氯嘧磺隆、绿磺隆、醚磺隆、甲磺隆、烟嘧磺隆、氯嘧磺隆、吡嘧磺隆、塞苯隆、醚苯磺隆、苯磺隆;硫代氨基甲酸酯类如苏达灭、草灭特、燕麦敌、扑草灭、禾草畏、草达灭、苄草丹、杀草丹、野麦畏;三嗪类如莠去津、草净津、西玛津、西草津、去草津、特丁津;三嗪酮如六嗪酮、苯嗪草、嗪草酮;其它类如氨基三唑、呋草磺、噻草平、恶庚草烷、广灭宁、Clopyralid、燕麦枯、氟硫草定、唑草定、氟咯草酮、草铵膦、草甘膦、异恶草胺、达草止、快杀稗、喹草酸、草硫膦、灭草环。
本制剂可含有单独的活性化合物或与其它可溶或不溶活性化合物组合的活性化合物。
本发明的制剂是通过简单混合而制备的,如果适宜可加热。
本发明的制剂可以浓缩物的形式直接使用或以植物保护组合物形式,或以口服、非肠道和经皮应用药剂的形式使用。在植物保护中,本制剂可用于叶面,土壤和杆茎部分施用和种子处理。
本发明的制剂分散入水相后,由于使用的聚合物(B)和表面活性剂(C)的性质,形成以高溶解性为显著特点的均相溶液或胶体分散液。这些水系统是制剂的使用形式。在此水性使用形式中活性化合物的浓度为0.0001-3%(重量),优选为0.001-2%(重量)。为了制备这种水溶液或水分散液,将本发明的制剂与所需要量的水相混合,如果适宜混合时可搅拌和/或泵送。在此不需要使用特殊的分散装置,如剪切式均浆器。
活性化合物(A)与聚合物(B)的比例可在很宽范围内变化,且通过初步试验可很容易地确定。通常,活性化合物与聚合物的重量比,以活性化合物为基础为1∶0.2-1∶10,优选为1∶0.2-1∶3。本发明制剂中其它添加剂的量可在相当宽的范围内变化。但是,对它们的调节应使制剂与水简单混合后形成的均匀溶液或胶体分散液的颗粒大小在0.01-0.4μm范围内,优选在0.03-0.2μm范围内。
下述实施例用于说明本发明
实施例1
将1份重量的硝苯吡酯,5份重量的30%(重量)的乙烯基吡咯烷酮和70%(重量)的乙酸乙烯酯的共聚物及0.225份重量的十二烷基硫酸钠溶于19份重量的乙醇(96%)中,将此浓缩物分散至225份重量的水中,对于此分散液,水相作为起始相,伴随搅拌将浓缩物快速加入。尽管使用的纯化形式的活性化合物和聚合物都是不溶于水的,但形成了清澈溶液,甚至在静置相当长的时间后,该溶液也不混浊。
溶解的活性化合物的含量确定是规定在室温下静置24小时,以测定在水分散液中活性化合物的结晶倾向。测定的方法如下:制备好分散液24小时后,取出该批的样品并通过0.45μm的滤器(商标Millipore)过滤以除去任何含有的结晶活性化合物(不能滤过的活性化合物)。将规定量的滤液溶于乙醇中并用光谱测定法确定活性化合物的含量。存在于溶解形式和/或胶体形式中的活性化合物的比例,可用实验确定的活性化合物含量与理论含量的相关联而确定。
24小时后滤过的活性化合物含量为所用浓度4mg/ml的82%。
对比实施例1
根据实施例1制备含有活性化合物的浓缩液,但是用等重量的溶于纯水的聚乙烯基吡咯烷酮(Luviskol K 30,BASF 出品)代替共聚物。刚刚制备完后,由于存在活性化合物的结晶,水相变得非常混浊。仅仅一小时后,结晶的活性化合物形成厚的沉淀,上清液清澈且几乎无色,从中可对活性化合物的结晶定量。制备24小时后,可滤过的活性化合物的含量为0%。
实施例2
将1份重量的硝苯吡酯,4份重量的20%(重量)的乙烯基吡咯烷酮和80%(重量)的乙酸乙烯酯的共聚物及0.225份重量的十二烷基硫酸钠溶于15份重量的乙醇(96%)中。将该浓缩物分散入225份重量的水中。对于此分散液,水相作为起始相,伴随搅拌将浓缩物快速加入。形成乳色的胶体分散液。甚至在静置24小时后,看上去仍没有变化。24小时后可滤过的活性化合物的含量为所用浓度4mg/ml的87%。
实施例3至7
将1份重量的硝苯吡酯,5份重量的按表1中的重量比制备的乙烯基吡咯烷酮和乙酸乙烯酯的聚合物及0.0113份重量的十二烷基硫酸钠溶于19份重量的乙醇(96%)中。按实施例1将此浓缩物分散入225份重量的水中。依据使用的聚合物的单体的比例,形成均匀的溶液或乳状的胶体分散液,它们在24小时后外观未发生变化,几乎定量形成结晶。表中列出了静置24小时后根据实施例1测定的可滤过的活性化合物的含量。发现随着乙酸乙烯酯含量的增加,共聚物的结晶抑制作用增强。可是,纯的乙酸乙烯酯不适于本发明制剂的制备。
对比实施例2
对比实施例2的分散液基本上根据DE 37 42 473 A1 的实施例1制备,但是二氢吡啶类活性化合物darodipine用硝苯吡酯代替。
将1g乙基纤维素N7(Dow Chemical)和0.4g硝苯吡酯溶于40ml 96%的乙醇中。在20℃,伴随剧烈搅拌将该溶液快速倒入200ml蒸馏水中。在50℃减压条件下,用5分钟在旋转蒸发器中蒸发掉乙醇。根据实施例1,在24小时后,通过0.45μm滤器过滤以确定活性化合物的含量,活性化合物的含量是理论最大含量的21%。
表1
实施例9
根据本发明,采用下表中列示的各成分量将活性成分(a.i.)[2-甲基-1-[[[1-(4-甲基苯基)乙基]氨基]羰基]丙基]氨基甲酸-1-甲基乙基酯配制成为有机浓缩物。用水稀释该浓缩物,获得半透明的胶体水分散液,该分散液稳定,不结晶和沉淀。如果不使用聚合物Luviskol VA
64.或用纯聚乙烯基吡咯烷酮如Luvisol K 30
代替,则用水稀释浓缩物得到混浊分散液,其中含有粗的颗粒,在数分钟内易形成沉淀。为了对比生物效果,根据同一表制备活性成分的标准悬浮浓液制剂。
本发明的制剂 | 标准制剂25%浓度可湿性粉剂 |
15%活性化合物 | 25%活性化合物 |
5%乳化剂1 | 16%乳化剂2 |
3%乳化剂2 | 5%乳化剂3 |
5%Luviskol VA 64 | 5% Ultrasil VN 3 |
%无水柠檬酸 | |
剩余物正甲基-吡咯烷酮 | 剩余物 Silltin Z |
乳化剂1 十二烷基苯磺酸单乙醇胺盐 乳化剂2 壬基酚10-乙二醇醚 乳化剂3 烷基芳基聚乙二醇醚 Ultrasil VN 3
高分散非晶态二氧化硅 Sillitin Z
颗粒状硅 Luviskol VA 64
乙烯基吡咯烷酮/乙酸乙烯酯(60/40)共聚物
生物效力的评价
为了测试本发明制剂中的药剂的活性,用不同浓度的制剂的水制备物,对番茄幼苗喷湿。为了对比,用标准制剂的水制备物单独处理一组番茄幼苗,其中活性成分有多种对比浓度。喷雾覆盖层干燥后,用番茄晚疫病(Phytophtera infestans)真菌的孢子的水悬液接种所有植物。将植物放置在20℃,100%相对湿度的温育室中。接种3天后,对植物的侵染进行评价,以观察活性成分浓度的作用。
在此试验中,本发明制剂开始作用的最小的活性成分浓度较之标准制剂低2倍。
实施例10
根据本发明,采用下表中表示的各成分的量,配制活性成分(a.i.)4-氯-N,3′-双(4-氯苯基)-4′,5′-二氢-(1,4′-二-1H-吡唑)-1-羧-酰胺的有机浓缩物。用水稀释浓缩物,获得半透明的胶体水分散液,该分散液稳定,不结晶及沉淀,如果不使用聚合物Luviskol VA
64,或用纯聚乙烯基吡咯烷酮如Luviskol K 30
代替,则用水稀释浓缩物得到混浊的分散液,其中含有粗的颗粒,并在数分钟内易于形成沉淀。为了对比生物效果,根据同样的表制备活性成分的标准悬浮浓液制剂。
本发明的制剂 | 标准制剂1:SC 200 | ||
溶剂: | 54.0%的N-甲基-吡咯烷酮 | 溶剂: | 20.0%的BP Enerthene2367 10.0%的丙二醇 |
乳化剂: | 13.0%的乳化剂1 | 乳化剂: | 5.0%乳化剂 PS 290.5% Renex 36 |
聚合物: | 13.4%的Luviskol VA 64 | 增稠剂: | 0.1% Kalzan S |
杀微生物剂: | 0.1%三氯酚 | ||
a.i.含量: | 20.0% | a.i.含量: | 19% |
剩余物: | 去离子水 |
生物效力的评价
a)辣根猿叶甲(Phaedon cochloeariae)
为了实验本发明制剂的药剂防治辣根猿叶甲的活性,将甘蓝(Brassia oleracea)叶在不同浓度制剂的水制备物中浸湿。为了对比,用标准制剂的水制备物单独处理叶片,其中采用对比浓度的活性成分。处理后,叶片用辣根猿叶甲幼虫侵染。7天后,评价幼虫的死亡率。本发明制剂与标准制剂相对生物效力比较的标准是发生50%死亡率(LD50)时的浓度比,它是根据下式确定的:相对生物效力=LD50(本发明)/LD50(标准制剂)。在本实验中,本发明制剂的相对效力超过8。
b)菜蛾(Plutella xylostella)
为了实验本发明制剂中的药剂防治菜蛾的活性,将甘蓝叶在不同浓度制剂的水制备物中浸湿。为了对比,用标准制剂的水制备物单独处理叶片,其中采用对比浓度的活性成分。处理后,用菜蛾的幼虫侵染叶片。7天后,根据实施例10a概括的方法评价幼虫的死亡率。
在本实验中,本发明制剂的相对效力是30。
c)草地粘虫(Spodoptera frugiperda)
为了实验本发明制剂中的药剂防治草地粘虫的活性,将甘蓝叶在不同浓度制剂的水制备物中学好湿。为了对比,用标准制剂的水制备物单独处理叶片,其中采用对比浓度的活性成分。处理后,用草地粘虫的幼虫侵染叶片。7天后,根据实施例10a概括的方法评价幼虫的死亡率。
在本实验中,本发明的制剂的相对效力是20。
d)烟芽夜蛾(Heliothis viriscens)
为了实验本发明制剂中的药剂防治烟芽夜蛾的活性,将甘蓝叶在不同浓度制剂的水制备物中浸湿。为了比较,用标准制剂的水制备物单独处理叶片,其中采用对比浓度的活性化合物。处理后,用烟芽夜蛾侵染叶片。7天后,根据实施例10a概括的方法评价夜蛾的死亡率。
在本实验中,本发明制剂的相对效力是7.5。
Claims (7)
1、活性化合物的胶体分散液剂,包括A组分-少量溶于水的活性化合物、B组分-乙烯基吡咯烷酮和/或乙烯基己内酰胺和至少一种降低聚合物水溶性的疏水的共聚单体的共聚物、组分C-一种或多种表面活性剂、如果适宜组分D和E-与组分A和B和C混溶的其它添加剂和/或稀释剂。
3、根据权利要求1的制剂,其特征在于疏水的共聚单体在共聚物中的重量含量为5-90%。
4、根据权利要求1的制剂,其特征在于组分A是选自下列物质的一种活性化合物:二氢吡啶类、吡咯类、硝基甲烷、芳基吡唑啉类、氨基甲酸缬氨酰胺、苯并噻吩甲酰胺和/或苯甲酰脲。
5、根据权利要求1的活性化合物制剂以浓缩物形式或用水稀释后用作药剂或植物保护组合物的应用。
6、含有根据权利要求1的活性化合物制剂的植物保护组合物水液。
7、含有根据权利要求1的活性化合物制剂的药剂水液。
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CN94117633A Expired - Fee Related CN1065110C (zh) | 1993-10-25 | 1994-10-25 | 活性化合物的胶体分散液剂 |
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Country | Link |
---|---|
EP (1) | EP0649649A3 (zh) |
JP (1) | JPH07233300A (zh) |
KR (1) | KR100348709B1 (zh) |
CN (1) | CN1065110C (zh) |
BR (1) | BR9404225A (zh) |
CZ (1) | CZ290281B6 (zh) |
DE (1) | DE4422881A1 (zh) |
FI (1) | FI944974A (zh) |
HU (1) | HU216063B (zh) |
IL (1) | IL111356A (zh) |
PL (1) | PL181029B1 (zh) |
SK (1) | SK127094A3 (zh) |
TW (1) | TW307659B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102264223A (zh) * | 2008-12-23 | 2011-11-30 | 巴斯夫欧洲公司 | 包含至少两种基本未混合的水凝胶的储存稳定凝胶配制剂 |
CN1871086B (zh) * | 2003-07-17 | 2012-02-15 | 旭化成医疗株式会社 | 金属胶体溶液 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5684121A (en) * | 1994-12-06 | 1997-11-04 | Isp Investments Inc. | N-vinyl lactam polymer containing tablets of low friability and high rate of dissolution |
CO4750754A1 (es) * | 1996-03-06 | 1999-03-31 | Novartis Ag | Composiciones microbicidas para plantas que contienen al menos fludioxonil y piroquinol, junto con un material portador apropiado. |
DE19753300A1 (de) * | 1997-12-01 | 1999-06-02 | Basf Ag | Verfahren zur Herstellung von festen Dosierungsformen |
TW581656B (en) * | 1999-11-08 | 2004-04-01 | Rohm & Haas | Stable dispersions of propanil |
DE10022990A1 (de) * | 2000-05-11 | 2001-11-22 | Aventis Cropscience Gmbh | Kombination von Pflanzenschutzmitteln mit Wasserstoffbrücken bildenden Polymeren |
DE10117049A1 (de) * | 2001-04-05 | 2002-10-17 | Novartis Ag | Zusammensetzung |
AU2007321357B2 (en) * | 2006-11-13 | 2012-06-14 | Basf Se | Application of block copolymers based on vinyl lactams and vinyl acetate as solubilizers |
US9006142B2 (en) | 2006-11-30 | 2015-04-14 | Basf Se | Agrochemical formulations comprising 1-vinyl-2-pyrrolidinone co-polymers |
MX2011011943A (es) | 2009-05-11 | 2011-11-29 | Basf Se | Polimeros para aumentar la movilidad de insecticidas poco solubles en el suelo. |
CN103890131A (zh) * | 2011-09-13 | 2014-06-25 | 路博润高级材料公司 | 表面活性剂响应性乳液聚合的微凝胶 |
US9714376B2 (en) * | 2011-09-13 | 2017-07-25 | Lubrizol Advanced Materials, Inc. | Surfactant responsive dispersion polymerized micro-gels |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4241048A (en) * | 1979-05-01 | 1980-12-23 | Bristol-Myers Company | Suspension composition of benzocaine |
FR2581541B1 (fr) * | 1985-05-09 | 1988-05-20 | Rhone Poulenc Sante | Nouvelles compositions pharmaceutiques permettant la liberation prolongee d'un principe actif et leur procede de preparation |
IL86211A (en) * | 1987-05-04 | 1992-03-29 | Ciba Geigy Ag | Oral forms of administration for carbamazepine in the forms of stable aqueous suspension with delayed release and their preparation |
AT391269B (de) * | 1988-12-30 | 1990-09-10 | Burghart Kurt | Pharmazeutische zubereitung |
DE69007886T2 (de) * | 1989-07-21 | 1994-11-17 | Izhak Blank | Östradiol enthaltende Mittel und Verfahren zur topischen Anwendung. |
-
1994
- 1994-06-30 DE DE4422881A patent/DE4422881A1/de not_active Withdrawn
- 1994-09-23 TW TW083108779A patent/TW307659B/zh active
- 1994-10-12 EP EP94116068A patent/EP0649649A3/de not_active Withdrawn
- 1994-10-19 SK SK1270-94A patent/SK127094A3/sk unknown
- 1994-10-21 PL PL94305542A patent/PL181029B1/pl unknown
- 1994-10-21 KR KR1019940027025A patent/KR100348709B1/ko not_active IP Right Cessation
- 1994-10-21 IL IL11135694A patent/IL111356A/en not_active IP Right Cessation
- 1994-10-21 FI FI944974A patent/FI944974A/fi unknown
- 1994-10-24 HU HUP9403066A patent/HU216063B/hu not_active IP Right Cessation
- 1994-10-24 CZ CZ19942625A patent/CZ290281B6/cs not_active IP Right Cessation
- 1994-10-24 BR BR9404225A patent/BR9404225A/pt not_active Application Discontinuation
- 1994-10-24 JP JP6282397A patent/JPH07233300A/ja active Pending
- 1994-10-25 CN CN94117633A patent/CN1065110C/zh not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1871086B (zh) * | 2003-07-17 | 2012-02-15 | 旭化成医疗株式会社 | 金属胶体溶液 |
CN102264223A (zh) * | 2008-12-23 | 2011-11-30 | 巴斯夫欧洲公司 | 包含至少两种基本未混合的水凝胶的储存稳定凝胶配制剂 |
Also Published As
Publication number | Publication date |
---|---|
CZ262594A3 (en) | 1995-05-17 |
CZ290281B6 (cs) | 2002-07-17 |
HU9403066D0 (en) | 1995-02-28 |
KR100348709B1 (ko) | 2002-10-31 |
HUT69064A (en) | 1995-08-28 |
DE4422881A1 (de) | 1995-04-27 |
IL111356A (en) | 1998-12-27 |
PL305542A1 (en) | 1995-05-02 |
HU216063B (hu) | 1999-04-28 |
SK127094A3 (en) | 1995-05-10 |
EP0649649A3 (de) | 1999-10-13 |
BR9404225A (pt) | 1995-07-04 |
EP0649649A2 (de) | 1995-04-26 |
JPH07233300A (ja) | 1995-09-05 |
PL181029B1 (pl) | 2001-05-31 |
TW307659B (zh) | 1997-06-11 |
FI944974A (fi) | 1995-04-26 |
FI944974A0 (fi) | 1994-10-21 |
IL111356A0 (en) | 1994-12-29 |
CN1065110C (zh) | 2001-05-02 |
KR950011537A (ko) | 1995-05-15 |
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